(1) Field of the Invention
This invention relates to polycyclic polyamines. More specifically, it relates to bicyclic and tricyclic trisaminomethanes, and to the method of their preparation.
(2) Description of the Prior Art
Polycyclic trisaminomethanes are known, but none in which the nitrogens are annular hetero atoms in a single large ring are known. The closest prior art references are:
1. Stetter and Bremen, Chem. Ber., 106, 2523 (1973), disclose the following reaction: ##STR3## in which R = CH.sub.3 or C.sub.6 H.sub.5 CH.sub.2
2. Leimgruber and Wick, U.S. Pat. No. 3,726,924 (Hoffmann-La Roche, 1973), discloses the reaction of dimethylformamide dimethyl acetal with excess dimethylamine in the presence of an acidic catalyst to give tris(dimethylamino)methane. EQU (CH.sub.3).sub.2 NH + HC(OCH.sub.3).sub.2 N(CH.sub.3).sub.2 .fwdarw. HC[N(CH.sub.3).sub.2 ].sub.3
3. bredereck et al., Chem. Ber., 101, 3058 (1968), disclose the preparation of tris(dialkylamino)methanes in which the alkyl groups are methyl, ethyl, and propyl by the reaction of the corresponding alkoxybis(dialkylamino)-methanes (aminal esters) with the dialkylamines: EQU (R.sub.2 N).sub.2 CHOR + R.sub.2 NH .fwdarw. (R.sub.2 N).sub.3 Ch + ROH
4. meerwein et al., Ann., 641, 1 (1961), disclose amine exchange between dimethylformamide diethyl acetal and piperidine or morpholine at 190.degree. C: ##STR4## Only the dimethylamino group reacts; the ethoxy groups are not replaced.